I haven’t written a blog post in a week. I travelled for a couple of days for work and decided to get some sleep on those days rather than staying up into the wee hours as I often do when I travel. I closed one deal (I’ll talk about that soon) and issued one term sheet (I hope to talk about that soon, we’ll see!). It has also coincided with the kickoff of our Launchpad LA educational series which has taken some of my time.

But what has really killed me is email. I live in email hell. And for the last few evenings I decided to get through email rather than blog. I’m always so completely behind on email. I have a love / hate relationship with email. Actually, mostly hate. Email is a chore. I’d much rather spend time conversing with people in a lighter weight venue. I’ve always been a big fan of IM (instant messaging) which is why Twitter has been so appealing to me. I love the restriction in terms of message size. And I find that platforms like Twitter, IM and even Facebook carry much less “obligation” to them. People expect too much when they email you. Your email is your recipients social obligation.

I email people – don’t get me wrong. It’s just that the whole email system seems to be out of balance. I’ve written about the topic before when I wrote the post “I emailed a VC but never heard back.” As in, what do you do now that you’ve written them. Should you bug them? Is it normal to not hear back? Are all VC’s just a-hole’s? If you’re interested in that topic have a read of my previous post.

It was interesting for me to read Fred Wilson’s email bankruptcy blog post this morning. I think I’m permanently bankrupt on email with no solution. I don’t think any GTD method will work. My volume is simply too big to handle. It’s like spaghetti – the more I process the more it seems there is. I’ve talked with a lot of VCs about this and all said the same thing, “we simply don’t get through it all. There’s no way to.” Actually, there is a way. If I never spent time with my wife & kids, which I’m not willing to do.

When I read Fred’s post it resonated for two reasons: 1. He ends up spending personal time trying to get through email. This is my life, too. And probably yours. We all want to be responsive people. 2. He makes in clear in his responses in the comments section that he wants to review the email directly himself where many people recommended an assistant read through it. I think we both feel we want to be accessible to people. Not all VC’s feel this way in my experience. Some love the filter. In my mind that’s OK for some people. It preserves more of their scarce time to deal with the people and companies with whom they want to interact. I’m on the side of wanting to be more accessible. It’s who I am.

But here’s the problem:

1. Anyone and everyone can email you. When email nomenclatures are obvious you’d be surprised how many people feel entitled to just email you. It’s not just the spammers or marketers trying to sell you products or services. I understand that. But it’s the person at undergrad who has a project in entrepreneurship and just wants your quick comments on their project. Really. I get those more often than you think. And when I have time I try to write back. Often I just can’t. It’s the alum from University of Chicago who realizes I got my MBA there and feels a sense of kinship. It’s the entrepreneur who’s buddy is a lawyer who wants an intro to you and who doesn’t think about whether it makes sense to ask you whether you want an intro before sending it. It’s all of these things accumulated that adds up to such a huge mass. And that’s in addition to portfolio companies, colleagues at work and legitimate deals you’re working on. It’s just too much cumulatively.

2. The sheer volume / math doesn’t work. If you think of it this way. Let’s assume I get 200 emails today. Let’s say I can delete 100 as unsolicited with just 5 seconds work / email. Then 30 are ones I can read quickly and delete or store (I only use one folder – “storage”) with no actions. Each of these takes 1 minute. Let’s say 30 are these sort of “unsolicited” emails that have some expected action associated with them. Let’s call these “optional” and if I get time they take 2 minutes each to read and respond. And then there are 30 “real” emails for which I really should read, process and come up with a sensible response. Let’s call these 3 minute emails. And the last 10 are the “big effort” emails. They’re from lawyers or CEO’s requiring analysis before a response. Let’s call these 10 minutes on average.

==> 3 hours, 40 minutes of email / day plus 1 hour of “optional” email. Let’s call it 4 hours. Who has 4 hours / day to process email? Let’s assume that I’m super efficient and can process these in 2 hours? Many days I have a breakfast meeting, back-to-back meetings all day and then an evening event. Or I’m at BOD meetings or conferences. I can normally “just about” manage my emails until I pile up 2 days traveling and then I have a crazy email traffic jam. If it’s more than 3 weeks old it’s unlikely that I’ll ever see it unless I search on it later (which is why I’ve started using X1 a lot more).

3. People who email you expect a response. Let’s face it. In the old days if you wrote people a physical letter, first it was a big effort to actually write and send the letter. So many things were filtered out. But second I think there wasn’t an expectation that people would write you back. Now everybody expects a response. Based on the email math problem this just isn’t realistic for many people.

4. I WANT to be responsive and open. I really do want to get back to everybody who writes to me. Sometimes I find myself trying to help the college student with a quick response. Sometimes I do offer that University of Chicago person some quick advice. So it really pains me that some people write me and I don’t write back. I don’t want to be “that guy” who doesn’t respond to emails so people think that I think I’m above it all. I’m not. I sometimes dread going to conferences where I know people will walk up to me and say, “I send you an email a few weeks ago” and I’m struggling to remember it. I have at least read or skimmed most of them. But not always.

5. Social networks exacerbate the problem. People now write me on Facebook, Twitter and LinkedIn. Luckily I haven’t signed up to Formspring and don’t spend time on Quora. I actually tell some people to write me on Twitter. Given that it’s constrained to 140 characters it’s easier to process. But there isn’t a permanent record or any way to “mark something as read” so some stuff falls through the cracks.

6. Blog comments. Why don’t you just blog less or not respond to everyone’s comments? I do get that sometimes from people. If I did that then I’d be letting email make me hostage to other people’s agendas. I enjoy the creative outlet of blogging and being able to build relationships with people in a lightweight way that often lead to in person meetings or phone calls down the line where appropriate.

Anyway, so for now I have to live with occasionally not living up to other people’s expectations. And to telling people to bug me multiple times if I haven’t responded to an email that they deemed as important. If that’s you – I apologize now, in advance. I’m willing to accept that I’ll never be a black belt in email.

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2x startup Founder & CEO who has gone to the Dark Side of VC. His first company, BuildOnline was sold in 2005, his second, Koral was acquired by Salesforce.com and became known as Salesforce Content, while Mark served as VP Product Management. In 2007 Mark joined GRP Partners in 2007 as a General Partner. He focuses on early-stage technology companies, usually looking at Series A investment, and blogs at the aptly titled Both Sides of the Table.